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Guthrie learned music from his father, who wrote songs for him like "Goodnight Little Arlo". When the young Guthrie became thirteen years old, his father gave him a Bar Mitzvah, and invited many folk musicians. It was called "the first hootenanny bar mitzvah in history."

Guthrie met Bob Dylan when Dylan came from Minnesota to meet his father Woody. Dylan taught Guthrie a new way to play the harmonica. Guthrie started college after high school, but dropped out.

During 1965, Guthrie visited his friends Alice and Ray Brock in Stockbridge, Massachusetts, who lived in an old church, and owned a restaurant. He recorded a musical commercial for the restaurant. When Thanksgiving came that year, they invited many people, and afterwards there was a lot of garbage to be picked up and thrown away. Guthrie and another friend tried to take the garbage to a dump, but it was closed. They found a large trash pile not far away, and unwisely decided to throw their garbage onto the same pile. (Dumping trash where it does not belong is called 'littering' and is a crime in most places.)

When local police found out, they arrested Guthrie and his friend. Since the young men had long hair and looked like hippies, the police wanted to prosecute them and make an example of them to other young people. They prepared a big court case against Guthrie and his friend, with many photographs of the litter pile. It turned out the local judge was blind, could not look at the photographs, and was not interested in the case. He fined Guthrie and his friend fifty dollars, and ordered them to clean up the pile.

Not long after, Guthrie received a draft notice. The United States Army wanted him to become a soldier. Guthrie went for a physical examination by a doctor, and had to fill out a questionnaire giving information about himself. When asked if he had ever been arrested, he talked about the littering incident. He soon found himself sitting on a bench together with criminals, some of which were violent or dangerous. He could not believe the way he was treated by the Army. He began to complain and protest his treatment. The Army officers decided he would not make a good soldier, but might become a threat to the American government. They fingerprinted Guthrie, and let him go.

Guthrie decided later the two incidents would make a good protest song and he built one around the jingle he had written. He called the song "Alice's Restaurant Massacree", and recorded it in front of a live audience. He did not want other young men to be drafted, and suggested in the song that they might get out of the draft by doing like he had.

The recording became half of his first album, and the rest was filled out with other music, like "The Motorcycle Song". The album became a hit record.

Guthrie later recorded other albums and songs. His cover of the Steve Goodman song, "The City of New Orleans", about a famous train named after the city, became another hit. He bought a farm with the money he earned from his music, and lived there between recording sessions and performing tours.

In time, he became interested in charity work. He noticed people of different religious beliefs did not always work well together for the same causes, because their beliefs kept them apart. He tried to work around the differences, and help people find ways to work together to solve the same problems. He started the Guthrie Center, as a place for people to work together. He later bought the old church where his friends had lived, and made it the headquarters for the Guthrie Center.